


Moving Up

by localchampion



Category: Impractical Jokers
Genre: Age Difference, F/M, Implied/Referenced Drug Use, Sex
Language: English
Status: Completed
Published: 2018-04-16
Updated: 2018-05-10
Packaged: 2019-04-23 23:02:15
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 8,780
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14342805
Author URL: https://archiveofourown.org/users/localchampion/pseuds/localchampion
Summary: A continuation of the relationship between James and Jaclyn from Real Estate.





	1. Chapter 1

**Author's Note:**

> If you haven't read Real Estate, I recommend it, just to get to know the characters. Enjoy!

The night James closed on his old apartment and finally got to kiss Jaclyn he made good on his offer to take her out to celebrate being done with selling his apartment. His hope all along was that maybe something more could develop between them now that they weren’t in a professional relationship.

They went to a nearby sushi restaurant for dinner and Jaclyn finally felt like she could let herself open up a bit more with James. He wasn't a client anymore, he was just another person, that she was into, and he seemed to be into her. When they finished their meal, she offered to give him a ride home since he had taken a cab to her office from the airport.

"Wanna come up and see the place? You haven't been over since I moved in."

"Oh yea, that's right, let's go" she said unbuckling her seat belt and following him in.

"This looks really, really good!" She exclaimed as they walked in. He showed her the kitchen, which he admitted was barely used, the office he had set up in the spare bedroom, the living room, and finally the bedroom up in the loft.

"Again, I'm very impressed with how you have this place decorated, you have great taste."

He smiled nervously and tilted his head to the side. "Thanks."

They stood close to each other just inside the door to his bedroom, the tension thick between them and neither exactly sure where things would go next until she glanced at the clock on his bedside table.

"Oh! I should be getting home I didn’t realize it was this late and I have early morning tomorrow. I had a really nice time tonight." She said reaching out and squeezing his arm as she leaned in to kiss his cheek.

"Yea, me too. Would you want to go out again maybe?" He asked hopefully.

"Yea, call me." She said with a smile as she saw herself out.

~

A couple days later, Jaclyn was sitting in her office when Victoria knocked on her door.

"Hey, you got a delivery!" She said with a knowing grin. Jaclyn furrowed her brow until Victoria pulled the bright bouquet from behind her back.

"Wow!" She said standing up, to take them from her assistant. "Who are they from?"

"I didn't open the card."

Jaclyn picked up the envelope which was already open. "Didn't open it huh?" She said raising an eyebrow.

"I think I hear the phone, excuse me!" She said turning and scurrying out.

Jaclyn rolled her eyes as she pulled out the small card that read 'Thank you again for all your hard work, you're the best. Are you busy on Friday? James'

She picked up her phone and closed her office door, as she imagined Victoria would be trying to eavesdrop. He didn't answer so she left him a voice mail.

"Hey James, thank you so much for the flowers, they are gorgeous! I'd love to go out of Friday, call me back or text me and we can set it up!"

She hung up and went back to admiring the flowers. She knew he was different from the other guys she dated and she was still reveling in the weak feeling she felt whenever she thought of their first kiss.

~

Later that day James called her back and they made plans to get dinner on Friday night. That entire week Jaclyn had more spring in her step waiting for the date night to arrive.

On Friday after work, she slipped into a knee length sleeveless black sheath dress with a knot detail above the left hip and then ran to her appointment to get a blowout. When she arrived at the restaurant, he was already outside waiting for her. He looked like a daydream in his well-tailored navy suit.

"Hey," she said getting out of the cab. "Hope you weren't waiting long."

"Not at all, you look great by the way." He said leaning in and pressing a kiss to her cheek. Jaclyn felt that melting feeling all over again, it was like his lips were her kryptonite.

"Thank you, so do you," she replied. "Wanna go in?" She said gesturing to the door of the restaurant.

"Yes, let's go it." He said opening the door for her.

They ordered their drinks and talked about the past week. She had a few big deals in the works, and was excited to be making even more of a name for company. He was excited that his show was in talks for another season and a movie deal.

“Well then I guess we toast to success!” She said raising her wine glass.

“And to this being a successful date?” He said hopefully.

“Oh I think so” she said smiling at him, holding his eye contact as they clinked glasses.

They continued chatting as they ate their meals. When the check was dropped off at the table, he paid and she wondered where the night was going to go next.

“Ready to go?” He asked.

“Sure, where to?”

“Come on,” he said with a mischievous grin. When they left the restaurant, he hailed a cab and they headed to midtown, finally stopping in front of Rockefeller Center.

“Have you ever been to the top?” He asked.

“No, I haven’t. To be honest, I haven’t been to many of the tourist spots. God, does this make me a bad New Yorker?” she asked with a laugh as they got out of the car.

“Nah, but I’m not surprised. This just gives you lots of new things to experience. Let’s go.” He said taking her hand. She grinned and followed him in.

He had purchased the tickets ahead of time and they got on the elevator up. No one else was in the elevator with them, and he decided to take advantage of the moment alone to gently place his hands on her cheek and pull her lips to his. She leaned into the kiss, deepening it until the bell of the elevator dinged and they were able to get off on to the observation deck.

“Wow, I’ve seen some beautiful views in this city, but this one is amazing!” She marveled. He smiled taking in the look of wonder on her face.

“Yea, we filmed up here a while back and I’ve been meaning to come back since then,” he replied.

James stepped closer behind her and put his hand on her waistline. It was then that he noticed she was shivering slightly in the cold night air. He took off his suit jacket and put it over her shoulders.

“Thanks” she said turning to look at him as she felt the weight of the material settle over her bare arms. She turned back to the view but leaned her back into him, his hands finding their way back to her waist again. After staying like this for a while, taking in the lights of the city laid out below them, James asked if she was ready to go. She nodded and they took the elevator back down, but they unfortunately did not get the elevator alone this time. When they were back at the street level, James hailed a cab to take her back home.

“I had a wonderful time,” Jaclyn said after getting out of the cab and he followed after walking her to the door of her building.

“I’m glad, I did too.” He said with a grin.

“So you’ll call and we’ll get together soon?” She asked as she slipped off his suit jacket that she had still been wearing, and handed it back to him.

“Of course,” he said leaning in and she leaned up to meet his kiss. She held his arms for support as she suddenly felt off balance by the warmth and affection of his kiss. When they finally separated, she waved at him and entered the building and he got back into the cab to go home. He pulled his jacket back on and could smell her lavender perfume on the lapel as he held it to his nose and sighed at the thought of the successful date.


	2. Chapter 2

**Notes for the Chapter:**

> Things are about to heat up. Enjoy!

Since their date, James and Jaclyn had been texting back and forth, but they had both gotten bogged down at their respective jobs. After a couple weeks since they last saw each other, James was filming at a mall in New Jersey. He felt his phone vibrate in his pocket and saw the message was from Jaclyn asking if he was free that evening and his heart skipped a beat. He knew he should have been trying harder with her or she might slip away, and now she was making an effort to see him. He couldn’t mess this opportunity up.

“How much longer do we have tonight?” James asked one of the producers.

“Why you got a hot date or something?” Q asked overhearing his question.

“Well yea, I’d like to,” James replied, exasperated.

“Well well well, is that so eh? Is it serious?” Q asked very interested to hear more. He glanced at James’s phone, which he had turned back to the home screen and noticed it looked different since the last time he saw it. “Wait did you even delete your dating apps?”

“What, you’re seeing someone?” Sal asked as he and Joe came over.

“Yea, but we haven’t seen each other in like 2 weeks.”

“Is it that pretty real estate agent that sold your place?” Joe asked, remembering the time he saw them meeting together at Starbucks.

“Yea” James replied, twitching his neck. He still just wanted to know when he could go.

“We’ll be done in about an hour,” the production assistant called over to them.

“Good because Murray’s gonna get some tonight!” Joe shouted back as James groaned and put his hands over his face.

Jaclyn was laying in bed, having spent a busy day showing an apartment that was a bit of a risk and she needed to unwind. She had texted James to see if he was finally free, and as much as she got a kick out of flirting with him via text message, she really wanted to see him. She had started to wonder that maybe the date wasn’t as successful as she thought since they hadn’t been able to make a second date happen yet. She wasn’t the type to chase after a guy, even if she really liked them, as she definitely preferred to be pursued, but she had had enough waiting for James and she wasn’t about to let whatever they may have fade away.

She didn’t realize she had dozed off until the sound of her phone going off woke her up. It was pitch black in her room, except the screen of her phone. She grabbed it, eyes adjusting to the light to see it was James.

“Meet me at 11?”

She glanced at the clock next to her bed, it was just past 9:30. “Yes! Where?” She replied. She pulled herself out of bed and went to her closet to pick out something to wear. He texted her back with a bar that she recognized wasn’t too far from his place. A thought crossed her mind that maybe there was a reason for that, and she put back the first dress she had picked out and pulled out a black dress with a v neck, and a short skirt that wrapped like a tulip in the front. She ran to her bathroom and touched up the makeup she hadn’t yet taken off from the day and refreshed her hair.

She hailed a cab and arrived promptly at the bar at 11. She spotted him at the far end of the bar, he stood up when he saw her walk in.

“Hey, it’s been too long!” She said as she walked up to him. He leaned in and gave her a kiss on the cheek.

“I’m so sorry I’ve been so busy lately. Thanks for coming out so late, I wanted to see you and the shoot ran long.”

“Don’t worry,” she replied putting her hand on his arm reassuringly. “I understand how it is. Not to sound too boring but I had already fallen asleep when you texted back!” She said with a laugh. He realized how he had missed that sound.

They ordered their drinks and retreated to a private table in a back corner of the bar to catch up on their lives. As they chatted and sipped their drinks, she kept her hand on his arm. Since it was Saturday night, the bar was full and they kept having to lean closer to each other to hear what they were saying over the buzz of the bar. After a couple more drinks, James’s hand found its way to her bare knee as she leaned herself into him more. After more flirting and close conversation, next thing she knew his lips were pressing against hers, then their tongues were sliding across each other. A few minutes later they separated and he took a quick inventory of their glasses and noticed they were both almost empty.

“Wanna get out of here?” He asked.

“Where to?” she asked, already knowing what he was going to suggest.

“My place?” He offered. She smiled and nodded as they gathered their things.

When they left the bar, he snaked his arm around her waist and kept pressing kisses to the side of her head as he held her close and she giggled. The walk to his apartment was only a few blocks, but by the time they made it into the elevator she could hardly take anymore. As the doors closed behind them, their lips were crashing together as he pressed her back against the wall of the elevator and she tried to pull him even closer to her by his shoulders.

They fumbled their way through his front door and she was already unbuttoning and pushing off his shirt. They finally landed on his plush couch and she found herself underneath him, her heart racing as he kissed her neck. His hands were roaming over her body and one slipped up her thigh under the hem of her skirt. He felt along the outside curve of her hip, but never ran into the feeling of fabric that he was expecting.

“Are you not…” He trailed off as she gave him an absolutely devilish grin as she shook her head. “Oh, you’re a dirty girl” he replied with an equally sinister grin.

“Only for you daddy” she replied, a little surprised at the words she just let slip from her lips. He looked just as surprised and equally enthralled as he slid his hand from her hip to between her thighs and she let out a gasp.

She pulled him back down to her and started kissing his neck until her concentration was broken by her own moans.

“Please, now” she begged and he pulled back to undo his belt and pants button. He grabbed his wallet and pulled out a condom and slipped it on before he pushed into her with a solid thrust and she let out another moan.

James leaned down and started to kiss her again as he kept up the strong thrusts and Jaclyn couldn’t believe how amazing he felt. She could feel herself building to her climax and she let out another moan.

“Oh, oh, yes, God yes, yes daddy I’m gonna come!”

“Yea, oh God, yea” he mumbled as he buried his face in the crook of her neck as he came. The sensation was enough to finish her off as well. He pushed himself back so he could look her in the eyes.

“God you’re beautiful” he murmured and she gave him a content smile.

“You’re pretty amazing yourself” she said reaching up and pulling his face back to her, kissing him deeply.

When they separated, he cleaned himself up and she pulled her skirt back down and righted herself on the couch.

“Can I get you something to drink?” He asked picking up his shirt from the floor. He pulled it on but left it unbuttoned.

“Yea, oh umm, coffee?” She asked, distracted by the sight.

He put a cup of coffee in the Keurig and she made her way to the kitchen. She hopped up on the counter and he handed her the mug of piping hot coffee as he made one for himself as well.

“You know, I was worried you weren’t that interested after our last date, but I guess that’s not true.” She said with a smile as she took a sip of her coffee.

“I’m sorry I ever made you think that. I would never want you to think I’m not interested. I really like you Jac.” James replied as he leaned against the counter next to where she was sitting.

“Good, I like you too, if you hadn’t noticed,” she said putting her hand on his arm reassuringly. He slid his arm back, taking her hand and placed a kiss on the back of it, and she blushed.

They talked in the kitchen while they finished their coffee, then they made their way back to the couch to keep talking, occasionally making out, and enjoying each other’s company. Before they realized it, the sun was starting to light up the dark sky outside the windows as they lounged with her legs over his lap, her head on his shoulder.

“God, is it really that late?” She asked when she noticed that it was about 6 AM.

“Could say it’s that early,” he replied with a shrug.

“Either way, it’s been a long time since I pulled an all-nighter. But it was worth it.”

“Me too” he replied kissing her.

They sat in silence for a while longer as the room continued to fill with light, her head resting on his shoulder.

“I’m not gonna let that happen again,” he mumbled to himself.

“Hmm?” She questioned, lifting her head.

“Sorry, I’m not gonna let things get in the way of us spending time together. Letting the last few weeks go by was a mistake. I promise to make more of an effort, as long as that’s what you want.”

“Yea, I want that.” she said leaning in to kiss him.


	3. Chapter 3

As spring warmed into summer, the relationship between James and Jaclyn continue to heat up. They both had careers that were a top priority and kept them very busy, but they were making more of an effort to spend time together, which meant meeting up for late night dinners after a long day of filming for him, attending parties so she could network and meet new potential clients, and if they only had a short amount of time, stopping off at each other’s apartments where things would inevitably get hot and heavy.

By the middle of the summer, James had finished filming the Impractical Jokers movie, and to celebrate him being back in New York full time, Jaclyn made reservations at a new restaurant that had just opened. They were enjoying their meal when two men approached their table.

"Jaaaaackie!" She closed her eyes and set her jaw at the sound of that voice slurring the nickname he knew she hated. James looked up at the man who had addressed Jaclyn. He looked like he was quite inebriated, and was being propped up by another man.

"Derek, it's been a while." Jaclyn sneered back. James was taken aback by the tone she took with this person, he’d never heard her that level of contempt come from her.

"Yea, how ya been? Who is this?" He asked leering at James.

"My date James. James, this is my ex Derek. Derek, so good to see you, have a good night." She said dismissively.

“James, my man, nice to meet you,” he said sticking out his hand to James, a look of amusement across his face. James narrowed his eyes and shook his hand. He glanced over at Jaclyn and saw how irritated she looked.

“Yea, same, but I think it is time you left,” James replied firmly.

A look of recognition crossed Derek's clouded eyes and he stood up straighter. "Oh, ok, yea I'll see you around Jackie." He said as he and his friend headed out.

Jaclyn let out a sigh and pinched the bridge of her nose once he was gone. "Sorry, he's such a mess. I dumped him last year when I found out about his coke habit. Clearly the party hasn't ended. Thanks, for getting rid of him. He knows I hate being called Jackie and he would do it just to get on my nerves."

"What a dick," James replied. "Wait, you don't mind when I call you Jac, do you?"

"No, I like that because I like you." She said with a smile for the first time since their meal had been interrupted.

“Good, because I don’t think I wanna get on your bad side,” he said with a laugh.


	4. Chapter 4

Jaclyn trudged wearily into her apartment. She had the day from hell and was only looking forward to getting dinner and spending some time with James. Her phone had almost run out of battery by about 3 PM, so she put it on the charger, but when she checked it a while later it was totally dead, the charger apparently no longer working. She plugged the phone in and pulled out a bottle of wine from the fridge. She poured a glass and went back to where the phone was charging to check her messages. The first was from James saying their shoot was not going well and was running long. They were supposed to be done by 6, and the message was from 6:45. Then another message at 8 saying they were almost done. She looked at the time it was almost 9.

“What the hell?” She muttered under her breath as she took a drink from her glass. She made her way over to the couch and opened her laptop to scroll through social media and emails. Before she realized it, an hour had passed. She went back over to where her phone was charging, she had no new messages.

“Are you still coming over?” She texted. A few moments later she got a response.

“Almost there.” She put her phone down and finished her wine and waited for him to arrive. When he finally rang her bell, he looked very tired.

“Hey, long day?” She asked as she let him in.

“It was awful, I just want to crash. I lost today so I’m gonna be getting punished, again. You’d think I’d get used to it eventually, but those assholes keep coming up with worse punishments every time.”

“So you don’t want to go get dinner?” She asked from where she was still standing by the door, purse in hand.

“Jac, it’s like 10, you haven’t had dinner?” He asked with a laugh, thinking she must be kidding.

“No, we were gonna go out, I waited for you.”

“I grabbed something on my way over here.” He replied as a look of annoyance washed over her face.

“Ugh, James” she whined. “I’m starving!”

“Well just order something for delivery, we can relax and watch a movie.” He replied, feeling the irritation with the situation rising. “Besides, you could have told me you were waiting.”

“My phone was dead! Ugh, whatever.” She muttered, letting the hanger and wine get the best of her tone.

“You don’t always have to be such a spoiled, helpless, upper east side princess you know!” He snapped.

Jaclyn’s eyes went wide and then narrowed at him. “Spoiled princess? Excuse me?” She practically shouted. “You know full well that I worked damn hard to get where I am! I am nowhere near helpless and if that’s what you think of me then maybe you don’t know me as well as you think you do! And maybe I don’t want you to know me any better than that.” She said crossing her arms defiantly across her chest. She didn’t mean it, but she was trying to prove a point.

“Jac, you know I didn’t mean it” James sighed, clearly exasperated by the situation, but she had already made her way back to her room and slammed the door. She knew pouting on her bed like a teenager wasn’t helping anything, but she didn’t care. She laid back on her bed wishing she had thought to grab her phone.

The next thing she knew she heard her front door shutting. She sat up realizing she had fallen asleep. She thought maybe he had decided to leave since she was being a brat in her room. She was relieved when she opened her door and saw James in the kitchen unloading a bag of food that had been delivered. He looked up when he heard her come in.

“I ordered lo mein, general tso’s chicken, fried rice and crab rangoons.”

“Thanks. And sorry for being a brat.” She replied.

“I’m sorry too. It was a shitty day, I shouldn’t have snapped. And besides if there’s anyone who deserves to be spoiled, it’s you, by me.” He said with a cheeky grin. Jaclyn smiled back and gave him a hug.


	5. Chapter 5

Summer was starting to wind down, and Jaclyn was getting ready for her annual week-long vacation at her family’s Southampton house. Her parents spent the majority of their summer there, but they always went away to Europe for a week and Jaclyn took advantage of that time to relax and unwind in one of her favorite places by herself. It also coincided with her oldest friend’s birthday party which was usually held at their family’s Southampton home as well.

“Hey sweetie, what’s up?” James asked when he picked up her call.

“Well, I was wondering what you’re doing the week of August 20th?”

After a moment of shuffling around noises, she heard him come back on, having put her on speaker. “I’ve got a lot of a meetings that week, but that weekend I’m free, what’s going on?”

“I’m going to be out in Southampton that week, I was wondering if you’d like to come along, maybe spend the weekend out there?”

“Yea, sounds like a nice vacation, I could come down after my last meeting on Friday” he replied.

“Great I’ll text you the address. There’s gonna be a party on Saturday night so pack a nice outfit too, ok?”

“Already looking forward to it!”

~

“Welcome, welcome!” She said opening the front door to the home. She was holding a small, squirming dog and even though she was on vacation, James wasn’t surprised to find her looking well put together in a white off the shoulder blouse and pink shorts that stood out against her tanned skin that proved that she had spent most of the week out in the sun.

“Hey, thank you for inviting me,” he said greeting her with a kiss. “Who is this?!” His voice jumping an octave as he addressed the dog, giving it a scratch behind the ears.

“This is Rosé, my mother’s dog! She’s a shih tzu and I love getting to watch her.” She said planting a kiss on the dog’s head. “Come on, let me give you the tour!”

He had to smile to himself as she went into realtor mode, something he hadn’t witnessed in quite a few months since when she was helping him find his apartment.

“My great-grandfather built this house in 1920. It was renovated and updated in the 1960’s by my maternal grandparents, and then renovated again about 15 years ago, which is what sparked my interest in design in the first place. We just redecorated again a couple summers ago, well I should say I redecorated, my mother left it completely up to me,” she said proudly as they moved from the living room to the dining room and kitchen.

“As you can see there’s a great backyard space, with a swimming pool, which is where I have been the past few days,” she said with a wave to the backyard as they went past the large back windows. “Let’s grab your bag and I’ll show you the rooms upstairs.”

“This is the master bedroom,” she said waving to a large room at the top of the stairs. “Then this over here is technically my sister’s room, however, she hasn’t been out her in years since she got married to a Silicon Valley genius and had a couple baby genius kids,” she said with a laugh. “And this is my room,” she said walking into her bright, sunny room and hopping onto the bed.

“This house is beautiful, you did a really great job with it,” he said as he sat down next to her on the bed.

“Thank you, I’m very proud of it. So I know of a nice little place to go get dinner tonight-” she started.

“Yea sure, that sounds good, but I have an idea for now” he said interrupted as he reached up and pulled her face to his, lips pressing together with a heat that matched the weather outside.

She let herself fall back on to her soft mattress and he followed after, holding himself up over her as they continued to make out. She slowly slid her hands up under his shirt, along the muscles he had been working on all summer, pulling his shirt off over his head. He started to kiss her neck and collarbones. She sat up so he could pull the blouse off over her head and continued kissing down the newly exposed skin to the button of her shorts. She lifted her hips as he undid the button and slid the shorts and panties off and as his hands slipped between her thighs, she let out a moan. She was the boss of her business, she was a go-getter, she worked hard and had her life together, but when he kissed her, she instantly felt herself surrendering to him. When he turned her on, she was completely under his control, putty in his hands.

“You like that?” He asked as his fingers nimbly working her into a frenzy.

“Mmm” she moaned. “Yes daddy, yes!”

He couldn’t wait much longer and quickly slid off his pants, slipped on a condom, and slid himself into her with a groan. “Oh baby, yea.”

They rocked together, pace and friction building until he felt himself getting close. He reached between them and her moans grew louder until she was shuddering in pleasure below him and he finished quickly after.

~

They spent the rest of the afternoon laying around the pool soaking up the sun and warm weather. Jaclyn reveled in her role of hostess as she put out a spread of food for them to enjoy. After they decided they were thoroughly baked in the sun, James insisted upon cleaning up while she slipped upstairs to take a quick shower and get ready for their evening.

They spent a wonderful night out getting dinner and drinks and walking around the town. As the sun started to set, they finally arrived back at her house and he made a fire in the backyard. They sat together in one of the Adirondack chairs and he held her close on his lap, reveling in the warm late summer evening.

“This is really nice,” he murmured.

“I agree, it’s been so long since I’ve been here with someone as special as you,” she replied kissing his cheek and he grinned. They sat together until the fire burned out and then they went up to her room to sleep.


	6. Chapter 6

The cool morning air filled the room the next day as Jaclyn and James let themselves sleep in, and then spent the rest morning having lazy, sleepy sex. They went out to brunch and then down the beach for a while in the afternoon. Upon returning home, they got ready for the birthday party for Jaclyn’s friend. Jaclyn got dressed in a flowy navy blue wrap dress with a white floral print that had a slit up the side to show her tanned leg, with her brown hair in waves down her back.

“Beautiful as always,” he said standing up as she came down the stairs to where he was waiting in the living room.

“Thank you babe,” she said as he took her hand and spun her around and she giggled. “Come on, let’s go.”

They arrived at the home that rivaled the home where James had been punished the summer before with the Olympic judoist. She strode into the house in her heels, the confidence exuding from her as she greeted other guests. James followed her through the house, proud to be with her.

“Fallon!” She squealed as she found the hostess of the party. They greeted each other with hugs and compliments on each other’s outfits.

“Fal, this is James, James this is Fallon. We’ve been friends since kindergarten and this is her family’s beautiful home that I again helped decorate.” Jaclyn explained with a proud grin. Jaclyn had a way of making Fallon and James feel like they had known each other as long as Fallon and Jaclyn had known each other. After the introductions and a brief conversation, Jaclyn and her friend finally slipped away when James got pulled into another conversation.

“He’s cuter than he is on TV, kind of a geeky Jason Statham kind of thing going on,” Fallon commented.

“I know right? I’ve dated older guys, but not a guy this much older than me. It’s definitely an improvement from any other guy I’ve been with. He's the funniest guy I've ever dated, and so smart and driven too.” Jaclyn replied contentedly.

“You seem very happy with him, is it loooove?” Asked Fallon with a laugh.

Jaclyn had been looking over at him and feeling her eyes on him, he looked over at her and shot her a smile. He was a gentleman, but his quick wit and sense of humor kept her on her toes. The way he made her feel when they were alone was unlike anything she had the pleasure of experiencing before. She knew from how he treated her that he cared about her, but she hoped he felt for as deeply for her as she did for him because she didn’t want to let him go. Jaclyn nodded in response to her question, a smile forming on her face. “Could be.”

“God, I love it. Does he have any cute single friends?” Fallon laughed again.

“A few, let me think about it a while, Jaclyn said slyly, taking a sip of her drink. She had met the other Jokers, and although she hadn’t immediately thought of any of them being a potential date for her friend, she hadn’t initially considered dating James when she first met him either.

"Perfect” her friend replied with a grin. “Do you feel like dancing? I do, let’s go!” She said as she grabbed Jaclyn’s arm and pulled her out onto the patio behind the house where the DJ was playing music and people were dancing.

After a while, the people James had been talking to had to leave, and he went to find where Jaclyn disappeared to. He followed the sound of the music out to the backyard of the beautiful home. He spotted her dancing with her friend, a carefree smile on her face. He watched her twirl around, her dress flowing around her, moving gracefully in her high heels, as easily as if she were barefoot. The moonlight shining off her hair, her eyes twinkling. He stood off to the side watching her having a great time with her friend for a few minutes. When the music switched from up-tempo to a slow song, "Stolen" by Dashboard Confessional, she looked around the crowd, a hopeful look on her face until she spotted him and waved him over.

Even though they had been together for several months now, the fact that she sought him out and picked him out of the crowd of people to dance with made his heart skip a beat. And this remarkable woman was the one he was going to get to go home with tonight, and wake up next to tomorrow. As he made his way past the other people dancing in the warm summer night, he realized that he didn’t want to ever go home with anyone else.

She smiled as he walked up to her and slipped her hand into his, as his other hand found her waist and they began to dance.

“Having a nice time?” She asked leaning into him.

“Yea, I’m glad I could come.”

“Me too” she said resting her head on his shoulder. He leaned his head against hers as they swayed together under the stars.


	7. Chapter 7

Summer cooled into fall, and Jaclyn’s mid-September birthday was just around the corner, and James wanted to make it a special day for her.

“What do you want to do for your birthday?” He asked one evening while they were walking back to her apartment after dinner. 

“I’m turning 32, that’s not really a milestone or anything. Just getting dinner with a couple friends would be nice.” She replied.

“Leave it to me then, I will plan you a birthday you won’t soon forget!” He replied with big smile.

“Is this one of your, what do you call them? Fool proof plans that always backfires on you?” She asked, teasing him, a sly smile playing on her lips.

“I really never should have lent you those DVDs of the show.” He muttered while tweaking his neck to the side and she just grinned.

“But if you hadn’t I wouldn’t have gotten to see that sexy speedo” she said with a giggle and he groaned at the embarrassing memory.

A couple weeks later on Jaclyn’s birthday she arrived at her office to find a large bouquet of deep pink roses from James already waiting on her desk. After work, she arrived at her favorite restaurant where James had made reservations and found him and Q were already waiting for her. James had invited a few of her friends, as well as the guys from the show, but only Q was able to make it. Jaclyn had made certain Fallon was going to be there because she had decided she wanted to set her up with Q.

“Hey guys!” She said as she walked up to them.

“Hey sweetie, happy birthday!” He said wrapping her in a big hug and planting a kiss on her that left her head spinning.

“Thanks” she said breathlessly when they separated. “Hey Q, thanks for coming!”

“Of course” he replied also giving her a hug.

Not too much later Victoria arrived, as well as Fallon, who Jaclyn promptly introduced to Q, and a couple other friends arrived shortly after. They were seated and had just placed their orders when Jaclyn looked up and groaned, which caused James to look up as well.

“Jackie, what are the odds?” Derek practically shouted as he approached the table.

“That I’d be at my favorite restaurant on my birthday, pretty good I’d say. What do you want Derek?” She asked, her voice dripping with venom.

“I just wanted to find you so I could tell you that I’m clean, you should come back to me” he said looming down at her in her chair.

“Which means your dealer got locked up and you’re clean until you can find another one, I’ve heard this all before,” she snapped back. “Please leave.”

“Come on Jackie, you don’t want to be here with him, come back with me” he started to protest, crouching down to her level and grabbing her hand in his. The other patrons of the restaurant started to look at the scene.

“Get your hands off her, she’s with me.” James said rising from his seat.

“Oh, you gonna make me?” Derek retorted standing back up, and with that Q also got up from his seat next to James to back him up.

“If I have to, yeah.” James said as he took a step toward Derek. Before anything more could happen, a waiter came up and told Derek he had to leave and pulled him along to the entrance.

“Oh my god” Jaclyn muttered, head in her hands, her face deep red with embarrassment. The restaurant which had become quiet watching the scene unfold burst back to life and eyes were no longer on their table, but Jaclyn could feel the tears welling up. Fallon noticed this and grabbed her purse and pulled Jaclyn with her to the bathroom.

“Ugh god, this is the worst” James said slouching back in his chair and Q sat down next to him. “I promised her a birthday she wouldn’t forget, but I didn’t mean like this!”

“Did you use the phrase fool proof plan?" Q asked, and James glared back. Q chuckled. "She’ll be ok buddy, don’t worry” Q said patting James' shoulder.

James leaned in to his friend’s ear so the others couldn’t hear and whispered “I was gonna tell her I loved her tonight, now it doesn’t seem right.” Q groaned and nodded acknowledgment.

“Probably best to wait.” he replied. They went back to talking to Jaclyn’s other friends who were very reassuring that this type of antic from Derek was not uncommon.

In the bathroom, Jaclyn was fixing her makeup after the tears left streaks down her cheeks.

“He’s such a god damn mess, he can’t think about anyone but himself, so much so that he has to try to ruin my birthday, oh my god, the nerve! I’m so embarrassed, James should never have been put in that situation, and he’s probably over me and my drama.” Jaclyn rambled as she rolled her eyes.

“But he stood up to him, like he was ready to old school fight for your honor! You got a gentleman there, you hang on to him!” Fallon replied.

Jaclyn sniffed her runny nose, and nodded. “Do I look ok?” she asked.

“Yea, you’re good” she said reassuringly. They walked back out to their table and they slipped back into their seats.

“Are you ok?” James asked leaning in so everyone wouldn’t hear.

“Yes, thank you for standing up for me” she said putting her hand on his arm. “Let’s talk about it later, I need a drink.” She said waving down the waiter and ordering another glass of wine. Their food came out shortly after and the rest of the dinner passed uneventfully. Everyone made sure to keep Jaclyn’s mind off the events earlier in the evening and she was very appreciative of that.

After they finished their meals, everyone went their separate ways, except for Fallon and Q who were going to get another drink together, which Jaclyn whispered to Fallon was exactly what she wanted for her birthday. James and Jaclyn got into a cab and decided to go back to his place, in case any unexpected visitors dropped by her apartment. When they were settled in, she let out a large sigh.

“I’m so, so sorry that he showed up again. I think that first time he saw us together it made him realize what he was missing out on, and yea” she trailed off, looking exhausted.

“It’s not your fault at all, you’re an amazing person, and I can’t blame him for being jealous” he said with a smile and a squeeze of her hand.

“Thank you again for standing up to him, he’s just so awful and he deserved to be put in his place.”

“Any time.” He replied. They sat in comfortable silence while they rode the rest of the way to his apartment. When they got up to his apartment she made her way to the living room, taking in the lights of the city below. She felt safe and protected up in his apartment. He dug into his jacket pocket and pulled out the small box containing the present he had purchased for her. When he walked into the living room he found her still standing in front of the large windows in the living room, a contented look on her face, despite the eventful dinner.

“Jac, wanna open your present?” He asked approaching her.

“Sure!” She replied.

“Happy birthday” He pulled the box from behind where he was holding it behind his back. She pulled the ribbon off and opened the box to find deep blue sapphire earrings.

“My birthstone and my favorite color! Thank you so much babe! They're absolutely perfect!” She said wrapping her arms around his neck and pulling him into a kiss. His hands wrapped around her waist and he deepened the kiss before he pulled back and took her hand, leading her to his bedroom.


	8. Chapter 8

The morning after her birthday dinner they were still laying in bed, both on their phones scrolling through their emails before they had to start their busy days.

"Babe, I was wondering if you would like to attend an event with me, if you aren't busy that night?" she asked curling herself against him.

"When is it?" He asked.

"October 19th. It's a charity gala."

"Oh cool,” he scrolled through his calendar to that day. “Yea I'm free that night. I always like the opportunity to dress up." He said with a grin. "How'd you hear about it?"

"My parents have a table at the event and I guess a couple had to cancel so a spot opened up and they offered it to us. Would it change your answer if I would have led with 'hey wanna meet my parents at a formal gala?'? Probably, so boom, negotiation skills." She said grinning up at him.

James sat up and tilted his head to the side nervously. "Jac, don't try to distract me with your negotiating skills! You’re sure this is how you want me to meet your parents?"

"Well, I was thinking about it. How better to make a first impression than at an event where you're already dressed nice, everyone is gonna be at least a little drunk, and there will be so many other people there, they won't hardly have time to talk to us at all. Trust me, that's how all these events go."

James sighed, he knew she was probably right. "Ok, I'll still go."

"I knew you would" she said leaning in and giving him a kiss.

~

The evening of the gala, James was dressed in his best tux and bow tie and went to pick up Jaclyn. He arrived at her door and rang the bell. A moment later she opened the door in a black floor length gown that had a plunging neckline, and small cutouts on the sides showing a sliver of skin still tan from the summer.

"Wow, you look gorgeous" he marveled, jaw dropped.

 “Thanks, you look great too,” she said reaching up to adjust his tie and pressing a quick kiss on his lips. “Ready to go?”

“Let’s go” he said offering her his arm. She slipped her arm through his and they headed down to the waiting car.

James was a little nervous as they rode quietly uptown in the backseat. She noticed he did is tale-tell head twitch a couple times while he stared at the traffic out the window.

“Hey,” she said reaching over and taking his hand. “It’s not that big of a deal, don’t worry. Just be your naturally charming self, you’ll be fine.” She smiled reassuringly.

He smiled back. “I just want to make a good impression.”

“You will. I already told them about you, it will be fine.”

They arrived at the venue where the gala was being held as wealthy people in their tuxes and gowns streamed in. Jaclyn found the her parents table where they were seated and they went and got drinks.

"I don't see them here yet, so you can relax," she said putting her hand on his arm.

"I'm fine" he replied taking a drink. They continued people watching and Jaclyn pointed out a few people she recognized.

"Oh there they are" Jaclyn pointed across the room to an older couple James recognized from the photos at the Southampton house. "Let's go say hello!"

James finished his drink and followed closely behind her as she moved breezily through the crowd, greeting people as she went.

"Hello," she said walking up behind her parents.  "Fancy seeing you here!" She said with a smile.

"Hi honey!" Her mom greeted her with a kiss on each cheek. Her dad gave her a stoic nod.

"I'd like to introduce you to my boyfriend, James. James, these are my parents, Jillian and Robert.”

"Nice to meet you" James said shaking her father's hand, then her mothers.

"Very nice to meet you dear, Jaclyn speaks very highly of you." Her mother said.

"Looks like they're about to start the meal, let's go sit." Her father said, leading the way to the table.

"I don't think he likes me very much" James whispered in Jaclyn’s ear as they followed them back to the table.

"That's just how he is. Everything is super serious, don't worry about it." She said brushing off his concern.

While they ate, James seemed to finally crack her father’s serious shell, and had everyone at the table laughing. During a lull in the conversation her mother leaned in and whispered in Jaclyn’s ear that she very much approved of James and she had a feeling her father did too. Jaclyn felt a blush over her cheeks. She was a grown woman, but knowing her mother liked him did matter to her.

After the meal and the speeches by all the important people from the charity, her mother and father excused themselves from the table to mingle other guests and the band started playing again.

“Would you care to dance?” James asked standing up and offering her his hand.

“Of course” she said standing up as well and following him out to the dance floor. “You seem much more relaxed now.”

“I am now that we’ve got those introductions out of the way.” They started dancing to the song that was being played, and after a couple songs the band began to play a slower song.

James slipped his hand onto her lower back and pulled her close. She placed her hand on his shoulder and her other hand in his as they swayed together. She found herself gazing into his eyes and she felt it. The way he treated her, the way he carried himself, it all came together in that moment, and those last fleeting doubts floated away. She knew what she was feeling for certain.

The rest of the party was a blur of dancing and drinks until they were back in the car on the way back to his apartment.

He woke up the next morning with her sleeping peacefully next to him, one hand against his chest, as if she was trying to keep him from slipping away from her.

Her hair was in her face and the makeup she didn't take off the night before was smudged under her eyes. He had always marveled at how polished, and professional she looked. Even at the summer house when she was in the pool, the hot sun practically melting them, she still looked put together. Now he could hardly believe how she looked so perfect, because she didn't look perfect. She was real, and remarkable. Her confidence not only in herself, but him as well was unwavering. He had had such a wonderful time with her the night before, her smile lit up the room, and her laugh was like music to his ears.

She started to stir and he reached over and brushed her hair out of her eyes.

"Morning" she murmured.

"Morning beautiful" he replied. She smiled sleepily.

"Did you enjoy yourself last night?" She asked.

"I had an amazing time with you."

She smiled even bigger as she shifted to prop herself up on her elbow. "You were an excellent date." She said leaning in to kiss him.

“Thank you. Jac, I was gonna tell you… a while ago, but it wasn’t right then. Jaclyn, I love you.” He stated looking deep in her eyes.

“I love you too James, I’ve never been more certain of anything.” She leaned in and pressed a deep kiss to his lips.

**Notes for the Chapter:**

> Thank you for reading the second part of the James and Jaclyn saga! Part 3 is on the way!


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